Estropipate

Estropipate
Clinical data
Trade names	Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
Other names	Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone
AHFS/Drugs.com	Monograph
Routes of; administration	By mouth
Drug class	Estrogen; Estrogen ester
ATC code	None;
Identifiers
	IUPAC name [(8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate; piperazine;
CAS Number	7280-37-7 ;
PubChem CID	5284555;
DrugBank	DB04574 ;
ChemSpider	4447610 ;
UNII	SVI38UY019;
KEGG	D00948 ;
ChEBI	CHEBI:4873 ;
ChEMBL	ChEMBL1200980 ;
CompTox Dashboard (EPA)	DTXSID3023005 ;
ECHA InfoCard	100.027.906
Chemical and physical data
Formula	C22H32N2O5S
Molar mass	436.56 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1;
	InChI InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1 ; Key:HZEQBCVBILBTEP-ZFINNJDLSA-N ;
(verify)

Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment of menopausal symptoms.[1][2][3][4] It is a salt of estrone sulfate and piperazine, and is transformed into estrone and estradiol in the body.[2][3] It is taken by mouth.[1]

Medical uses

Estropipate is used to:[1]

Alleviate symptoms of menopause as menopausal hormone therapy
Treat some types of infertility
Treat some conditions leading to underdevelopment of female sexual characteristics
Treat vaginal atrophy
Treat some types of breast cancer (particularly in men and postmenopausal women)
Treat prostate cancer
Prevent osteoporosis

Estrogen dosages for menopausal hormone therapy
Route/form	Estrogen	Low	Standard	High
Oral	Estradiol	0.5–1 mg/day	1–2 mg/day	2–4 mg/day
	Estradiol valerate	0.5–1 mg/day	1–2 mg/day	2–4 mg/day
	Estradiol acetate	0.45–0.9 mg/day	0.9–1.8 mg/day	1.8–3.6 mg/day
	Conjugated estrogens	0.3–0.45 mg/day	0.625 mg/day	0.9–1.25 mg/day
	Esterified estrogens	0.3–0.45 mg/day	0.625 mg/day	0.9–1.25 mg/day
	Estropipate	0.75 mg/day	1.5 mg/day	3 mg/day
	Estriol	1–2 mg/day	2–4 mg/day	4–8 mg/day
	Ethinylestradiol^a	–	5–15 μg/day	–
Nasal spray	Estradiol	150 μg/day	300 μg/day	600 μg/day
Transdermal patch	Estradiol	25 μg/day^b	50 μg/day^b	100 μg/day^b
Transdermal gel	Estradiol	0.5 mg/day	1–1.5 mg/day	2–3 mg/day
Vaginal	Estradiol	25 μg/day	–	–
Vaginal	Estriol	30 μg/day	0.5 mg 2x/week	0.5 mg/day
IM or SC injection	Estradiol valerate	–	–	4 mg 1x/4 weeks
	Estradiol cypionate	1 mg 1x/3–4 weeks	3 mg 1x/3–4 weeks	5 mg 1x/3–4 weeks
	Estradiol benzoate	0.5 mg 1x/week	1 mg 1x/week	1.5 mg 1x/week
SC implant	Estradiol	25 mg 1x/6 months	50 mg 1x/6 months	100 mg 1x/6 months
Footnotes: ^a = No longer used or recommended, due to health concerns. ^b = As a single patch applied once or twice per week (worn for 3–4 days or 7 days), depending on the formulation. Note: Dosages are not necessarily equivalent. Sources: See template.

Available forms

Estropipate is available in the form of 0.75, 1.5, 3, and 6 mg oral tablets.[5]

Pharmacology

Pharmacodynamics

Estropipate is a prodrug of estrone and estradiol. Hence, it is an estrogen, or an agonist of the estrogen receptors.

Estropipate has been found to act as an inhibitor of SLCO1B1 (OATP1B1) (IC₅₀ = 70 nM).[6]

Relative oral potencies of estrogens
Estrogen	Type	HF	VE	UCa	FSH	LH	HDL-C	SHBG	CBG	AGT	Liver
Estradiol	Bioidentical	1.0	1.0	1.0	1.0	1.0	1.0	1.0	1.0	1.0	1.0
Estrone	Bioidentical	?	?	?	0.3	0.3	?	?	?	?	?
Estriol	Bioidentical	0.3	0.3	0.1	0.3	0.3	0.2	?	?	?	0.67
Estrone sulfate	Bioidentical	?	0.9	0.9	0.8–0.9	0.9	0.5	0.9	0.5–0.7	1.4–1.5	0.56–1.7
Conjugated estrogens	Natural	1.2	1.5	2.0	1.1–1.3	1.0	1.5	3.0–3.2	1.3–1.5	5.0	1.3–4.5
Equilin sulfate	Natural	?	?	1.0	?	?	6.0	7.5	6.0	7.5	?
Ethinylestradiol	Synthetic	120	150	400	60–150	100	400	500–600	500–600	350	2.9–5.0
Diethylstilbestrol	Synthetic	?	?	?	2.9–3.4	?	?	26–28	25–37	20	5.7–7.5
Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: HF = Clinical relief of hot flashes. VE = Increased proliferation of vaginal epithelium. UCa = Decrease in UCa. FSH = Suppression of FSH levels. LH = Suppression of LH levels. HDL-C, SHBG, CBG, and AGT = Increase in the serum levels of these liver proteins. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (specifically hot flashes relief and gonadotropin suppression). Type: Bioidentical = Identical to those found in humans. Natural = Naturally occurring but not identical to those found in humans (e.g., estrogens of other species). Synthetic = Man-made, does not occur naturally in animals or in the environment. Sources: See template.

Pharmacokinetics

Estropipate is hydrolyzed into estrone in the body.[7] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.

Chemistry

History

Estropipate was introduced for medical use by Abbott in 1968.[8] It was approved by the FDA in the United States in 1991.[9]

Society and culture

Generic names

Estropipate is the generic name of the drug and its INN, USAN, and BAN.[2][3][10][7][11]

Brand names

Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[11][2][10][7]

Availability

Estropipate appears to remain available only in the United States.[11] In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.[11][10][7]

References

https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf
J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1.
William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3.
Joseph T. DiPiro; Robert L. Talbert; Gary C. Yee; Gary R. Matzke, Barbara G. Wells, L. Michael Posey (23 January 2017). Pharmacotherapy: A Pathophysiologic Approach, Tenth Edition. McGraw-Hill Education. p. 1295. ISBN 978-1-259-58749-8.CS1 maint: multiple names: authors list (link)
http://www.fasebj.org/cgi/content/meeting_abstract/23/1_MeetingAbstracts/748.2
Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2101. ISBN 978-0-85369-840-1.
Penny Wise Budoff (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
P & T. CORE Medical Journals. July 1993.
Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
https://www.drugs.com/international/estropipate.html

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[OgenLabel-1] ttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf

[Elks2014-2] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.

[MortonHall2012-3] I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1.

[Publishing2013-4] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3.

[DiPiroTalbert2017-5] Joseph T. DiPiro; Robert L. Talbert; Gary C. Yee; Gary R. Matzke, Barbara G. Wells, L. Michael Posey (23 January 2017). Pharmacotherapy: A Pathophysiologic Approach, Tenth Edition. McGraw-Hill Education. p. 1295. ISBN 978-1-259-58749-8.CS1 maint: multiple names: authors list (link)

[FASEBJ-6] ttp://www.fasebj.org/cgi/content/meeting_abstract/23/1_MeetingAbstracts/748.2

[Martindale-7] Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2101. ISBN 978-0-85369-840-1.

[Budoff1983-8] Penny Wise Budoff (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.

[CORE1993-9] P & T. CORE Medical Journals. July 1993.

[IndexNominum2000-10] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.

[Drugs.com-11] ttps://www.drugs.com/international/estropipate.html

Estradiol
Topics	Estradiol (as a hormone) Estradiol (as a medication) Pharmacodynamics of estradiol Pharmacokinetics of estradiol Estrogen (as a hormone) Estrogen (as a medication) Menopausal hormone therapy Transgender hormone therapy (male-to-female) Estradiol-containing birth control pill Combined injectable birth control High-dose estrogen Hydroxylation of estradiol
Esters	Estrogen ester Estradiol ester Estradiol acetate Estradiol benzoate Estradiol benzoate butyrate Estradiol cypionate Estradiol dipropionate Estradiol enantate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estramustine phosphate (estradiol normustine phosphate)
Related	Estrone Estriol Estetrol Ethinylestradiol Conjugated estrogens Esterified estrogens Estrone sulfate Estropipate (piperazine estrone sulfate)